# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_js1119a
_database_code_depnum_ccdc_archive 'CCDC 1975376'
loop_
_audit_author_name
_audit_author_address
'Ajay Kumar Chinnam'
;University of Idaho
United States of America
;
_audit_update_record             
;
2020-01-04 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;
_audit_creation_date             2019-11-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N10 O4, 2(H5 N2)'
_chemical_formula_sum            'C4 H12 N14 O4'
_chemical_formula_weight         320.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.63810(10)
_cell_length_b                   13.5120(2)
_cell_length_c                   10.66810(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.2230(10)
_cell_angle_gamma                90
_cell_volume                     1244.88(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5073
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      68.41
_cell_measurement_theta_min      5.12
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.649
_exptl_absorpt_coefficient_mu    1.287
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0626 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.8697. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 0.00 0.1290
0.00 1.00 -1.00 0.0560
0.00 -1.00 1.00 0.0230
-1.00 -1.00 0.00 0.1080
1.00 1.00 0.00 0.1700
1.00 -1.00 -1.00 0.1300
0.00 -1.00 -1.00 0.0100
0.00 1.00 1.00 0.0320
1.00 -1.00 0.00 0.1390
0.00 0.00 1.00 0.0130
-1.00 1.00 -1.00 0.1070

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10664
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.400
_diffrn_reflns_theta_min         5.121
_diffrn_ambient_temperature      173.0(10)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1956
_reflns_number_total             2288
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.3355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0885
_refine_special_details          
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which was found 
by difference Fourier methods and refined isotropically.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67911(12) 0.71320(8) 0.73162(11) 0.0245(3) Uani 1 1 d . . . . .
O2 O 0.50874(14) 0.60544(9) 0.79180(10) 0.0283(3) Uani 1 1 d . . . . .
O3 O 0.13319(14) 0.36335(9) 0.64687(11) 0.0291(3) Uani 1 1 d . . . . .
O4 O 0.05672(14) 0.37021(9) 0.45212(11) 0.0305(3) Uani 1 1 d . . . . .
N3 N 0.33380(14) 0.60517(9) 0.44225(11) 0.0161(3) Uani 1 1 d . . . . .
N1 N 0.33153(15) 0.51540(9) 0.61477(12) 0.0182(3) Uani 1 1 d . . . . .
N14 N 0.02452(16) 0.33807(10) 0.16596(13) 0.0187(3) Uani 1 1 d . . . . .
N2 N 0.22598(14) 0.53482(9) 0.41785(12) 0.0182(3) Uani 1 1 d . . . . .
N5 N 0.56632(14) 0.65550(9) 0.70708(12) 0.0179(3) Uani 1 1 d . . . . .
N10 N 0.17241(14) 0.71042(10) 0.18474(12) 0.0196(3) Uani 1 1 d . . . . .
N7 N 0.36119(15) 0.60634(10) 0.14201(12) 0.0203(3) Uani 1 1 d . . . . .
N6 N 0.13365(15) 0.40034(10) 0.54170(12) 0.0201(3) Uani 1 1 d . . . . .
N11 N 0.68137(16) 0.55277(10) 0.12039(12) 0.0200(3) Uani 1 1 d . . . . .
N8 N 0.26307(15) 0.61246(10) 0.04301(12) 0.0209(3) Uani 1 1 d . . . . .
N9 N 0.15077(15) 0.67458(10) 0.06860(12) 0.0214(3) Uani 1 1 d . . . . .
N4 N 0.51588(14) 0.65665(10) 0.59021(12) 0.0186(3) Uani 1 1 d . . . . .
N12 N 0.72277(17) 0.62729(11) 0.02980(14) 0.0257(3) Uani 1 1 d . . . . .
N13 N 0.01184(17) 0.44457(10) 0.17758(15) 0.0251(3) Uani 1 1 d . . . . .
C4 C 0.30207(16) 0.66654(11) 0.22699(14) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.23219(17) 0.48568(11) 0.52412(13) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.39703(16) 0.59320(11) 0.55907(13) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.37374(19) 0.68368(12) 0.35311(14) 0.0209(3) Uani 1 1 d . . . . .
H11A H 0.703(2) 0.4898(16) 0.084(2) 0.037(6) Uiso 1 1 d . . . . .
H13A H 0.065(2) 0.4698(16) 0.121(2) 0.032(5) Uiso 1 1 d . . . . .
H11B H 0.579(2) 0.5580(14) 0.1365(17) 0.022(5) Uiso 1 1 d . . . . .
H14A H -0.008(2) 0.3221(13) 0.0894(18) 0.019(4) Uiso 1 1 d . . . . .
H14B H -0.039(2) 0.3067(15) 0.2206(19) 0.030(5) Uiso 1 1 d . . . . .
H14C H 0.121(2) 0.3124(15) 0.1820(18) 0.028(5) Uiso 1 1 d . . . . .
H12A H 0.706(3) 0.6849(19) 0.068(2) 0.048(7) Uiso 1 1 d . . . . .
H13B H 0.056(2) 0.4593(15) 0.251(2) 0.031(5) Uiso 1 1 d . . . . .
H12B H 0.648(2) 0.6205(15) -0.032(2) 0.031(5) Uiso 1 1 d . . . . .
H3A H 0.484(2) 0.6856(15) 0.3486(18) 0.030(5) Uiso 1 1 d . . . . .
H3B H 0.339(2) 0.7439(15) 0.3888(17) 0.024(5) Uiso 1 1 d . . . . .
H11C H 0.733(2) 0.5614(16) 0.186(2) 0.035(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N5 1.2707(17) . ?
O2 N5 1.2414(17) . ?
O3 N6 1.2283(17) . ?
O4 N6 1.2220(17) . ?
N3 N2 1.3523(18) . ?
N3 C1 1.3596(18) . ?
N3 C3 1.4706(19) . ?
N1 C2 1.3406(19) . ?
N1 C1 1.339(2) . ?
N14 N13 1.4487(19) . ?
N14 H14A 0.885(19) . ?
N14 H14B 0.91(2) . ?
N14 H14C 0.91(2) . ?
N2 C2 1.314(2) . ?
N5 N4 1.3121(18) . ?
N10 N9 1.3396(18) . ?
N10 C4 1.3370(19) . ?
N7 N8 1.3426(18) . ?
N7 C4 1.328(2) . ?
N6 C2 1.448(2) . ?
N11 N12 1.4458(19) . ?
N11 H11A 0.95(2) . ?
N11 H11B 0.91(2) . ?
N11 H11C 0.83(2) . ?
N8 N9 1.3158(19) . ?
N4 C1 1.3729(19) . ?
N12 H12A 0.89(3) . ?
N12 H12B 0.92(2) . ?
N13 H13A 0.84(2) . ?
N13 H13B 0.88(2) . ?
C4 C3 1.487(2) . ?
C3 H3A 0.95(2) . ?
C3 H3B 0.95(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N3 C1 110.75(12) . . ?
N2 N3 C3 123.56(12) . . ?
C1 N3 C3 125.69(12) . . ?
C1 N1 C2 100.66(12) . . ?
N13 N14 H14A 107.4(12) . . ?
N13 N14 H14B 111.0(13) . . ?
N13 N14 H14C 115.6(12) . . ?
H14A N14 H14B 106.9(17) . . ?
H14A N14 H14C 110.5(17) . . ?
H14B N14 H14C 105.1(17) . . ?
C2 N2 N3 100.01(12) . . ?
O1 N5 N4 115.22(12) . . ?
O2 N5 O1 120.11(12) . . ?
O2 N5 N4 124.62(13) . . ?
C4 N10 N9 104.53(12) . . ?
C4 N7 N8 104.70(12) . . ?
O3 N6 C2 117.11(13) . . ?
O4 N6 O3 124.50(14) . . ?
O4 N6 C2 118.39(13) . . ?
N12 N11 H11A 107.2(13) . . ?
N12 N11 H11B 109.2(12) . . ?
N12 N11 H11C 109.0(15) . . ?
H11A N11 H11B 110.2(17) . . ?
H11A N11 H11C 111.1(19) . . ?
H11B N11 H11C 110.1(18) . . ?
N9 N8 N7 109.38(12) . . ?
N8 N9 N10 109.49(12) . . ?
N5 N4 C1 117.00(12) . . ?
N11 N12 H12A 104.7(15) . . ?
N11 N12 H12B 103.3(13) . . ?
H12A N12 H12B 107.5(19) . . ?
N14 N13 H13A 107.2(15) . . ?
N14 N13 H13B 105.5(13) . . ?
H13A N13 H13B 108.1(18) . . ?
N10 C4 C3 124.44(14) . . ?
N7 C4 N10 111.90(13) . . ?
N7 C4 C3 123.66(14) . . ?
N1 C2 N6 120.94(13) . . ?
N2 C2 N1 119.00(14) . . ?
N2 C2 N6 120.06(13) . . ?
N3 C1 N4 115.54(13) . . ?
N1 C1 N3 109.57(13) . . ?
N1 C1 N4 134.74(14) . . ?
N3 C3 C4 111.95(12) . . ?
N3 C3 H3A 107.5(12) . . ?
N3 C3 H3B 106.1(11) . . ?
C4 C3 H3A 110.8(12) . . ?
C4 C3 H3B 111.5(11) . . ?
H3A C3 H3B 108.9(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H11A N8 0.95(2) 1.96(2) 2.8790(19) 160.3(18) 3_665 yes
N11 H11B N7 0.91(2) 1.99(2) 2.8729(19) 162.8(17) . yes
N14 H14A N9 0.885(19) 2.067(19) 2.9020(18) 156.9(16) 3_565 yes
N14 H14B N10 0.91(2) 2.02(2) 2.9191(18) 166.9(18) 2_545 yes
N14 H14C O1 0.91(2) 1.97(2) 2.8475(17) 159.9(18) 3_666 yes
N14 H14C O3 0.91(2) 2.41(2) 2.8875(18) 112.9(15) 4_565 yes
N12 H12A O1 0.89(3) 2.24(3) 3.0753(19) 156(2) 4_575 yes
N11 H11C N1 0.83(2) 2.44(2) 2.9760(18) 122.8(18) 3_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N5 N4 C1 178.16(12) . . . . ?
O2 N5 N4 C1 -4.1(2) . . . . ?
O3 N6 C2 N1 7.6(2) . . . . ?
O3 N6 C2 N2 -172.96(14) . . . . ?
O4 N6 C2 N1 -172.67(14) . . . . ?
O4 N6 C2 N2 6.8(2) . . . . ?
N3 N2 C2 N1 -0.21(17) . . . . ?
N3 N2 C2 N6 -179.70(12) . . . . ?
N2 N3 C1 N1 -0.57(16) . . . . ?
N2 N3 C1 N4 175.59(12) . . . . ?
N2 N3 C3 C4 -9.7(2) . . . . ?
N5 N4 C1 N3 171.68(12) . . . . ?
N5 N4 C1 N1 -13.4(2) . . . . ?
N10 C4 C3 N3 99.03(17) . . . . ?
N7 N8 N9 N10 -0.11(17) . . . . ?
N7 C4 C3 N3 -81.91(18) . . . . ?
N8 N7 C4 N10 -0.56(16) . . . . ?
N8 N7 C4 C3 -179.72(13) . . . . ?
N9 N10 C4 N7 0.50(17) . . . . ?
N9 N10 C4 C3 179.65(14) . . . . ?
C4 N10 N9 N8 -0.23(16) . . . . ?
C4 N7 N8 N9 0.40(16) . . . . ?
C2 N1 C1 N3 0.39(15) . . . . ?
C2 N1 C1 N4 -174.73(16) . . . . ?
C1 N3 N2 C2 0.45(15) . . . . ?
C1 N3 C3 C4 170.98(13) . . . . ?
C1 N1 C2 N2 -0.12(18) . . . . ?
C1 N1 C2 N6 179.37(13) . . . . ?
C3 N3 N2 C2 -179.00(13) . . . . ?
C3 N3 C1 N1 178.87(13) . . . . ?
C3 N3 C1 N4 -5.0(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id AKC-15A
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shrv813
_database_code_depnum_ccdc_archive 'CCDC 1985501'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2020-02-21 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N9 O2, H4 N O'
_chemical_formula_sum            'C4 H8 N10 O3'
_chemical_formula_weight         244.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.2376(3)
_cell_length_b                   7.3733(5)
_cell_length_c                   15.1316(10)
_cell_angle_alpha                96.429(3)
_cell_angle_beta                 94.148(3)
_cell_angle_gamma                96.090(3)
_cell_volume                     465.46(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2783
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      74.81

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.292
_shelx_estimated_absorpt_T_min   0.758
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5674
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   '1uS microfocus'
_diffrn_radiation_monochromator  'Montel multilayer optics'
_diffrn_measurement_device_type  'Photon II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3092
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.949
_diffrn_reflns_theta_max         74.798
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.802
_diffrn_measured_fraction_theta_full 0.854
_diffrn_reflns_Laue_measured_fraction_max 0.802
_diffrn_reflns_Laue_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.802
_diffrn_reflns_point_group_measured_fraction_full 0.854
_reflns_number_total             1531
_reflns_number_gt                1441
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+0.1605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'instrinsic phasing'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1531
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9918(3) 1.03975(17) 0.81498(9) 0.0393(4) Uani 1 1 d . . . . .
O2 O 1.2547(3) 0.96695(18) 0.93091(9) 0.0393(4) Uani 1 1 d . . . . .
N3 N 1.0469(3) 0.93425(18) 0.86940(9) 0.0259(4) Uani 1 1 d . . . . .
C4 C 0.8563(4) 0.7569(2) 0.85988(10) 0.0211(4) Uani 1 1 d . . . . .
N5 N 0.9039(3) 0.63664(18) 0.91833(9) 0.0225(3) Uani 1 1 d . . . . .
C6 C 0.6852(4) 0.4952(2) 0.88565(10) 0.0203(4) Uani 1 1 d . . . . .
N7 N 0.6361(4) 0.33788(19) 0.92000(10) 0.0298(4) Uani 1 1 d . . . . .
H7A H 0.7521 0.3198 0.9682 0.036 Uiso 1 1 calc R U . . .
H7B H 0.4876 0.2515 0.8946 0.036 Uiso 1 1 calc R U . . .
N8 N 0.5240(3) 0.53896(17) 0.81123(8) 0.0193(3) Uani 1 1 d . . . . .
N9 N 0.6375(3) 0.71115(17) 0.79360(9) 0.0227(3) Uani 1 1 d . . . . .
C10 C 0.2866(3) 0.4251(2) 0.74788(10) 0.0205(4) Uani 1 1 d . . . . .
H10A H 0.1373 0.5036 0.7221 0.025 Uiso 1 1 calc R U . . .
H10B H 0.1626 0.3349 0.7795 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4440(3) 0.3251(2) 0.67417(10) 0.0192(3) Uani 1 1 d . . . . .
N12 N 0.6134(3) 0.40859(18) 0.61610(9) 0.0224(3) Uani 1 1 d . . . . .
N13 N 0.7278(3) 0.27105(18) 0.56643(9) 0.0245(3) Uani 1 1 d . . . . .
N14 N 0.6275(3) 0.11365(18) 0.59347(9) 0.0253(3) Uani 1 1 d . . . . .
N15 N 0.4455(3) 0.14295(18) 0.66179(9) 0.0233(3) Uani 1 1 d . . . . .
O16 O 0.1537(3) -0.21403(17) 0.65080(8) 0.0310(3) Uani 1 1 d . . . . .
H16 H 0.231(6) -0.087(3) 0.6622(16) 0.046 Uiso 1 1 d . U . . .
N17 N -0.1033(3) -0.23179(18) 0.58399(9) 0.0246(3) Uani 1 1 d . . . . .
H17A H -0.0288 -0.2513 0.5292 0.037 Uiso 1 1 calc R U . . .
H17B H -0.1998 -0.1270 0.5880 0.037 Uiso 1 1 calc R U . . .
H17C H -0.2465 -0.3285 0.5918 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.221(2) . ?
O2 N3 1.2191(19) . ?
N3 C4 1.4491(19) . ?
C4 N9 1.305(2) . ?
C4 N5 1.340(2) . ?
N5 C6 1.3430(19) . ?
C6 N7 1.326(2) . ?
C6 N8 1.362(2) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N8 N9 1.3708(18) . ?
N8 C10 1.4618(18) . ?
C10 C11 1.503(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.336(2) . ?
C11 N15 1.336(2) . ?
N12 N13 1.3471(18) . ?
N13 N14 1.312(2) . ?
N14 N15 1.3458(19) . ?
O16 N17 1.4163(18) . ?
O16 H16 0.95(3) . ?
N17 H17A 0.9100 . ?
N17 H17B 0.9100 . ?
N17 H17C 0.9100 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N3 O1 124.42(14) . . ?
O2 N3 C4 117.44(14) . . ?
O1 N3 C4 118.13(14) . . ?
N9 C4 N5 118.97(14) . . ?
N9 C4 N3 120.38(15) . . ?
N5 C4 N3 120.65(14) . . ?
C4 N5 C6 101.41(13) . . ?
N7 C6 N5 125.42(15) . . ?
N7 C6 N8 125.56(14) . . ?
N5 C6 N8 109.02(14) . . ?
C6 N7 H7A 120.0 . . ?
C6 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C6 N8 N9 110.46(12) . . ?
C6 N8 C10 129.59(13) . . ?
N9 N8 C10 119.62(13) . . ?
C4 N9 N8 100.14(13) . . ?
N8 C10 C11 110.76(12) . . ?
N8 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N8 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N12 C11 N15 111.86(14) . . ?
N12 C11 C10 123.97(13) . . ?
N15 C11 C10 124.07(15) . . ?
C11 N12 N13 104.54(13) . . ?
N14 N13 N12 109.45(13) . . ?
N13 N14 N15 109.65(12) . . ?
C11 N15 N14 104.49(13) . . ?
N17 O16 H16 107.1(14) . . ?
O16 N17 H17A 109.5 . . ?
O16 N17 H17B 109.5 . . ?
H17A N17 H17B 109.5 . . ?
O16 N17 H17C 109.5 . . ?
H17A N17 H17C 109.5 . . ?
H17B N17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 C4 N9 -177.63(14) . . . . ?
O1 N3 C4 N9 1.5(2) . . . . ?
O2 N3 C4 N5 1.7(2) . . . . ?
O1 N3 C4 N5 -179.19(14) . . . . ?
N9 C4 N5 C6 -0.44(18) . . . . ?
N3 C4 N5 C6 -179.79(13) . . . . ?
C4 N5 C6 N7 179.51(15) . . . . ?
C4 N5 C6 N8 0.02(15) . . . . ?
N7 C6 N8 N9 -179.13(14) . . . . ?
N5 C6 N8 N9 0.36(16) . . . . ?
N7 C6 N8 C10 -5.9(2) . . . . ?
N5 C6 N8 C10 173.61(13) . . . . ?
N5 C4 N9 N8 0.64(17) . . . . ?
N3 C4 N9 N8 179.99(13) . . . . ?
C6 N8 N9 C4 -0.57(15) . . . . ?
C10 N8 N9 C4 -174.59(12) . . . . ?
C6 N8 C10 C11 -88.86(18) . . . . ?
N9 N8 C10 C11 83.86(16) . . . . ?
N8 C10 C11 N12 -63.1(2) . . . . ?
N8 C10 C11 N15 113.17(16) . . . . ?
N15 C11 N12 N13 -0.81(17) . . . . ?
C10 C11 N12 N13 175.88(13) . . . . ?
C11 N12 N13 N14 0.61(16) . . . . ?
N12 N13 N14 N15 -0.22(17) . . . . ?
N12 C11 N15 N14 0.69(17) . . . . ?
C10 C11 N15 N14 -176.01(13) . . . . ?
N13 N14 N15 C11 -0.28(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7A N5 0.88 2.14 2.9916(19) 161.7 2_767
N7 H7B O1 0.88 2.61 3.4826(19) 170.5 1_445
N7 H7B O2 0.88 2.36 3.0531(18) 135.7 1_445
C10 H10A O16 0.99 2.45 3.260(2) 139.1 1_565
C10 H10B O1 0.99 2.35 3.277(2) 155.2 1_445
O16 H16 N14 0.95(3) 2.48(3) 3.2114(19) 133.4(19) .
O16 H16 N15 0.95(3) 1.84(3) 2.7688(18) 165(2) .
N17 H17A N13 0.91 2.00 2.876(2) 160.9 2_656
N17 H17B N14 0.91 1.99 2.8927(19) 174.6 1_455
N17 H17C N12 0.91 2.05 2.899(2) 155.3 1_445

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.062


# start Validation Reply Form
_vrf_PLAT029_shrv813             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.854 Why?  
RESPONSE: Low data completeness is often encountered in triclinic unit 
cells when utilizing Cu radiation.
;
_vrf_PLAT430_shrv813             
;
PROBLEM: Short Inter D...A Contact  O2       ..O2       .       2.80 Ang.  
RESPONSE: High density energetic materials often display close contacts.
;
_vrf_PLAT911_shrv813             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        245 Report
RESPONSE: Low data completeness is often encountered in triclinic unit 
cells when utilizing Cu radiation.
;
# end Validation Reply Form
